Triethylamine → 4-(4,4-Dimethyl-5-imino-2-oxo-1-imidazolidinyl)-2-trifluoromethyl-benzonitrile

HRID 1919297ノート

反応式

HRID 1919297 の反応式
[NH2:1][C:2]([CH3:6])([CH3:5])[C:3]#[N:4].C(N(CC)CC)C.[N:14]([C:17]1[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[C:19]([C:25]([F:28])([F:27])[F:26])[CH:18]=1)=[C:15]=[O:16]>ClCCCl>[CH3:5][C:2]1([CH3:6])[C:3](=[NH:4])[N:14]([C:17]2[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[C:19]([C:25]([F:26])([F:27])[F:28])[CH:18]=2)[C:15](=[O:16])[NH:1]1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 880222-Amino-2-methylpropionitrileHCID 110637394-Isocyanato-2-(trifluoromethyl)benzonitrile

生成物 1

HCID 221169484-(4,4-Dimethyl-5-imino-2-oxo-1-imidazolidinyl)-2-trifluoromethyl-benzonitrile収率 47.3%

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒2 回

反応条件

温度
0 °C

実験手順

To a solution of compound 9 (641 mg, 7.62 mmol) and triethylamine (168 mg, 1.66 mmol) in 1,2 dichloroethane (8.4 mL) at 0° C. under argon was dropwise added a solution of the isocyanate 8a (1.54 g, 7.28 mmol) in 1,2 dichloroethane (3.5 mL). The solution was stirred at 0° C. for 35 min and the ice bath was then removed and stirred at room temperature for an additional 30 min. The solution was then evaporated to dryness and purified by flash chromatography using EtOAc/Hexane (6:4) as an eluant to give pure compound 10a (1.02 g, 47%). 1H NMR (300 MHz, Acetone-d6) δ: 1.54 (m, 6H), 7.45 (broad s, 1H), 8.12 (d, 1H, J=8.46 Hz), 8.29 (dd, 1H, J1=6.90 Hz, J2=1.61 Hz), 8.46 (s, 1H), 8.51 (s, 1H).

後処理

  1. customthe ice bath was then removed
  2. stirringstirred at room temperature for an additional 30 min
  3. customThe solution was then evaporated to dryness
  4. custompurified by flash chromatography

出典と根拠

ORDレコード
ord-2ea9b9cc3a25451b94dd4117a7368cd1
出典データセット
uspto-grants-2012_05
特許番号
US08168627B2

反応ノート

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